Giant molecular spoked wheels in giant voids: two-dimensional molecular self-assembly goes big

Tahara, Kazukuni; Lei, Shenbin; Mössinger, Dennis; Kozuma, Hiroyoshi; Inukai, Koji; Auweraer, Mark Van der; Schryver, F. C. De; Höger, Sigurd; Tobe, Yoshito; Feyter, Steven De

doi:10.1039/b806444j

Cited by 58 publications

(48 citation statements)

References 40 publications

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“…[23] Today, molecular-resolution imaging by scanning tunneling microscopy (STM) enables the monitoring of the assembly of macrocyclic p-systems on surfaces. [32][33][34] Most importantly, the inspiration provided by the 2D networks 2 and 3 has led to a renaissance of annulene chemistry, half a century after the seminal work by Sondheimer and co-workers. [35][36][37][38][39][40] In fact, a variety of benzannellated dehydro [12]-and [18] annulene-derived substructures of graphyne [30,41] and graphdiyne [42][43][44] have been prepared, such as 4-9 ( Fig.…”

Section: Introductionmentioning

confidence: 98%

“…1), and the physical, in particular the optoelectronic properties of the parent and peripherally functionalized compounds have been investigated; [45][46][47] this work has been the subject of several recent reviews. [30,31,39,48] Appropriate peripheral decoration also enhances the self-assembly properties [33,34,49] of such shape-persistent macrocycles. [50][51][52] Continuing interest exists in probing the aromaticity [53] and antiaromaticity of these dehydroannulenes and other macrocyclic p-systems both experimentally and by advanced theoretical calculations.…”

Section: Introductionmentioning

confidence: 99%

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All‐Carbon Scaffolds by Rational Design

2010

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The search for new molecular and regular polymeric allotropes of carbon has greatly stimulated the preparation and investigation of pi-conjugated acetylenic macrocycles, which often represent substructures of proposed 2D carbon networks. Perethynylated dehydroannulenes, expanded radialenes, and radiaannulenes with large, multi-nanometer-sized all-carbon cores are potent electron acceptors, and their optoelectronic as well as stability and solubility properties are greatly enhanced by peripheral donor substitution. Acetylenic scaffolding into three dimensions has generated an expanded cubane with a C(56) core, the first representative of a new class of "platonic" objects. Exceptional chiroptical properties displayed by enantiomerically pure alleno-acetylenic, shape-persistent macrocycles promise fascinating perspectives for the development of molecular and supramolecular chiroptical materials.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

All‐Carbon Scaffolds by Rational Design

2010

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“…31 This limitation was overcome by introduction of geometrical kinks by inserting a diacetylene unit, which served like a harness to bind long alkyl chains, at proper positions in the alkyl chain as in DBA-DAOC24OC25 and DBA-DAOC32OC33 (Figure 8). …”

Section: ¹1mentioning

confidence: 99%

Adaptive Building Blocks Consisting of Rigid Triangular Core and Flexible Alkoxy Chains for Self-Assembly at Liquid/Solid Interfaces

Tobe¹,

Tahara²,

Feyter³

2016

Bulletin of the Chemical Society of Japan

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has been a full professor since 2011 at KU Leuven-University of Leuven in Belgium. After starting up scanning tunneling microscopy during his Ph.D. in the group of Prof. Frans C. De Schryver at KU Leuven he moved for a postdoctoral position to the group of Prof. Ahmed Zewail (Caltech) where he was involved in ultrafast organic femtochemistry. His current interests include the study of supramolecular chemistry and self-assembly phenomena at surfaces, including modification of 2D materials, with a focus on liquid-solid interfaces. In 2013, he was awarded an ERC advanced grant. AbstractSupramolecular self-assembly in two-dimensional (2D) spaces on solid surfaces is the subject of intense current interest because of perspectives for various applications in nanoscience and nanotechnology. At the liquid/graphite interface, we found by means of scanning tunneling microscopy molecules with a rigid triangular core, a twelve-membered annulene (DBA), substituted by six flexible alkoxy chains selfassembled to form hexagonal porous 2D molecular networks via van der Waals interactions between interdigitated alkyl chains as the directional intermolecular linkages. Factors that affect the formation of the porous 2D molecular networks including alkyl chain length, solvent, solute concentration, and temperature were elucidated through a systematic study. Because DBA molecules are versatile for chemical modification, they turned out to be highly adaptive for on-surface supramolecular chemistry with respect to (i) pore size control by changing the chain length, (ii) study of parity effect due to even or odd number chains, (iii) generation of supramolecular chirality on surfaces by introducing stereocenters, (iv) chemical modification of the pore interior for selective co-adsorption of guest molecules by introducing functional groups. Additionally, formation of superlattice structures on surfaces was incidentally observed by mixing DBAs of different alkoxy chain parity or by addition of guest molecules via an induced-fit mechanism. These results made significant contribution to advancement of supramolecular chemistry in 2D space.

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“…At high concentrations the arms of the molecule overlapped eliminating the pores [101]. They further demonstrated that a large polycyclic compound that resembled a wagon wheel would selectively fill 7 nm voids in this two-dimensional annulene structure [102].…”

Section: From Liquid Phase To Solid Interfacesmentioning

confidence: 96%